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3-Hydroxy-2-nitrobenzaldehyde

  • CAS No. 42123-33-1

  • Cat. No. CS-0102239
  • Purity≥97%
  • MDL No.MFCD09753744

*For research and further manufacturing use only, not for direct human use.

3-Hydroxy-2-nitrobenzaldehyde|CS-0102239

Structure of 42123-33-1

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General Information

  • CAS No. 42123-33-1
  • Cat. No. CS-0102239
  • Purity ≥97%
  • MDL No. MFCD09753744
  • Storage 4°C, stored under nitrogen
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₇H₅NO₄
  • Molecular Weight 167.12
  • Synonym(s) None
  • SMILES O=CC1=CC=CC(O)=C1[N+]([O-])=O

Description

3-Hydroxy-2-nitrobenzaldehyde features a strategically positioned hydroxyl group adjacent to an electron-deficient nitro-substituted aromatic ring, enabling unique reactivity in transition metal-catalyzed couplings. This ortho-hydroxy nitroaromatic aldehyde integrates readily into complex molecular architectures, offering enhanced solubility and stability under standard bench conditions.

Application

3-Hydroxy-2-nitrobenzaldehyde serves as a versatile building block in medicinal chemistry and materials science, enabling efficient access to functionalized heterocycles via condensation and cyclization reactions. Its ortho-hydroxyl and nitro groups facilitate chelation and directed metalation, enhancing regioselectivity in electrophilic substitutions. The aldehyde functionality supports facile derivatization through imine formation, reductive amination, or oxidative transformations. Bench-stable and readily purified by recrystallization, it functions as a reliable scaffold for synthesizing bioactive molecules and advanced ligands.

Synthesis

  • Route1

    References

    • Just,G.; Zamboni,R. Canadian Journal of Chemistry, 1978 , vol. 56, p. 2725 - 2730
  • Route2
    • 3-Hydroxybenzaldehyde Roxatidine Impurity|CS-0229483
      100-83-4
    • ~%
    • In-stock
      3-Hydroxy-2-nitrobenzaldehyde|CS-0102239
      42123-33-1

    References

    • Hodgson; Beard Journal of the Chemical Society, 1925 , vol. 127, p. 876,877 Journal of the Chemical Society, 1926 , p. 150 Full Text Show Details Hodgson; Smith Journal of the Chemical Society, 1937 , p. 76
  • Route3

    References

    • Meshram; Ganesh; Madhavi; Eshwaraiah; Yadav; Gunasekar Synthetic Communications, 2003 , vol. 33, # 14 p. 2497 - 2503

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

  • TPSA   80.44
  • LogP   1.1129
  • H_Acceptors   4
  • H_Donors   1
  • Rotatable_Bonds   2

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